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Relative Unidirectional Translation in an Artificial Molecular Assembly Fueled by Light

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† †Department of Chemistry, ‡Department of Chemistry and Argonne-Northwestern Solar Energy Research Center, and §Department of Materials Science and Engineering, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
∥ State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, PR China
⊥ Materials and Process Simulation Center, California Institute of Technology, Pasadena, California 91125, United States
# Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371
○ School of Materials Science and Engineering, Nanyang Technological University, 50 Nanyang Avenue, Singapore 639798
⧫ National Center for Nano Technology Research, King Abdulaziz City for Science and Technology, P.O. Box 6086, Riyadh 11442, Kingdom of Saudi Arabia
Intel Labs, Building RNB-6-61, 2200 Mission College Boulevard, Santa Clara, California 95054, United States
+ NanoCentury KAIST Institute and Graduate School of EEWS (WCU), Korea Advanced Institute of Science and Technology (KAIST), 373-1 Guseong Dong, Yuseong Gu, Daejeon 305-701, Republic of Korea
◊ Department of Physics, The University of Maine, 5709 Bennett Hall, Orono, Maine 04469-5709, United States
[email protected]
Cite this: J. Am. Chem. Soc. 2013, 135, 49, 18609–18620
Publication Date (Web):October 30, 2013
https://doi.org/10.1021/ja4094204
Copyright © 2013 American Chemical Society
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    Abstract

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    Motor molecules present in nature convert energy inputs, such as a chemical fuel or incident photons of light, into directed motion and force biochemical systems away from thermal equilibrium. The ability not only to control relative movements of components in molecules but also to drive their components preferentially in one direction relative to each other using versatile stimuli is one of the keys to future technological applications. Herein, we describe a wholly synthetic small-molecule system that, under the influence of chemical reagents, electrical potential, or visible light, undergoes unidirectional relative translational motion. Altering the redox state of a cyclobis(paraquat-p-phenylene) ring simultaneously (i) inverts the relative heights of kinetic barriers presented by the two termini—one a neutral 2-isopropylphenyl group and the other a positively charged 3,5-dimethylpyridinium unit—of a constitutionally asymmetric dumbbell, which can impair the threading/dethreading of a [2]pseudorotaxane, and (ii) controls the ring’s affinity for a 1,5-dioxynaphthalene binding site located in the dumbbell’s central core. The formation and subsequent dissociation of the [2]pseudorotaxane by passage of the ring over the neutral and positively charged termini of the dumbbell component in one, and only one, direction relatively defined has been demonstrated by (i) spectroscopic (1H NMR and UV/vis) means and cyclic voltammetry as well as with (ii) DFT calculations and by (iii) comparison with control compounds in the shape of constitutionally symmetrical [2]pseudorotaxanes, one with two positively charged ends and the other with two neutral ends. The operation of the system relies solely on reversible, yet stable, noncovalent bonding interactions. Moreover, in the presence of a photosensitizer, visible-light energy is the only fuel source that is needed to drive the unidirectional molecular translation, making it feasible to repeat the operation numerous times without the buildup of byproducts.

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    Detailed synthesis procedures and characterization (NMR and HRMS) data for all compounds. Spectroscopic (NMR and UV/vis) and electrochemical (CV) characterization of the pseudorotaxane complexes. This material is available free of charge via the Internet at http://pubs.acs.org.

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